


If You Want A Good Wingman, Join The Air Force

by seriousfic



Category: Arrow (TV 2012)
Genre: Crack, Double Dating, F/M, Fluff and Crack, Season/Series 01
Language: English
Status: In-Progress
Published: 2014-09-17
Updated: 2014-09-18
Packaged: 2018-02-17 19:51:48
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,443
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2321318
Author URL: https://archiveofourown.org/users/seriousfic/pseuds/seriousfic
Summary: <blockquote class="userstuff">
              <p>Does it count as a double date if two of the people are only there to make sure the other two get laid?</p>
            </blockquote>





	1. Chapter 1

John Diggle came down the stairs to Verdant’s basement, finding things as normal as they could be in his boss’s secret lair from which he plotted his vigilante war on crime. Felicity was still trying to crack a particularly thorny site’s firewall, while Ollie was doing things to a punching bag that it surely didn’t deserve.

 

“Alright, superfriends,” Diggle called, loosening his tie now that he was in private. “What’s on the agenda tonight?”

 

“Tonight?” Ollie showed his punching bag mercy. “I thought you had your date with Carly tonight?”

 

“Not that we were paying attention or anything.” Diggle glanced over at Felicity, catching her just as she was swiveling her head back to her 1080p screen.

 

“Yes,” Diggle said, “I do have a date tonight, but there’s time enough to cancel it if something’s come up. So has something?”

 

“Hmmm?” Ollie asked innocently.

 

“Come up? No crazed terrorists trying to blow up a building? No one-percenter about to dump toxic waste in the harbor? No international assassin in town to make a hit?”

 

“The only thing getting hit tonight is—whatever nightspot you and Carly choose to hit up,” Ollie recovered. It’d been five years, but the douchebag in him was hard to kill. He started toweling himself off. “And since we’re not at full strength, I thought we’d give crime the night off. The List will hold till tomorrow. Go on your date. Have fun.”

 

“You’re sure?” Diggle demanded. “Because it’s no trouble.”

 

“Hey, Dig, you yourself said I can’t do this every night. _Go._ Me and Felicity are just gonna have a nice quiet night in. I’ll do some training, show her a few moves, it’ll be fun.”

 

“And if anyone robs a bank, we can handle it,” Felicity assured him. “Ollie can handle it. I can be assistant-handler—of it.”

 

Duty-bound, Diggle was about to launch another complaint, but he had been wanting to go on this date with Carly for a while. He’d already put it off once… “If you’re sure?”

 

“Positive. One of us deserves to have a social life.”

 

“Alright then.” Diggle straightened his tie. “Good night Oliver, good night Felicity, let’s pick this up tomorrow.” With that, he climbed the stairs.

 

“Go get ‘em, tiger!” Felicity cheered, but Diggle mercifully shut the door behind him, pretending he hadn’t heard. “By the way, Oliver, I do have a social life.”

 

“I can believe it.” He quickly crossed over to her workstation. “You worked up that profile on Carly?”

 

“All finished. Every Facebook post, tagged photo, bulletin board account—even her Youtube comments. Don’t worry, she just left a bunch of messages about how videos of baby animals make her heart do things.”

 

“Good. I bugged her jewelry. Let’s take this to the streets.”

 

Felicity nodded, though she wasn’t sure what that meant in this context. “Oliver, are you sure he needs our help? I mean, he’s a pretty handsome guy and—“

 

“Felicity, game recognizes game.” Oliver tapped his chest. “And Dig is looking very unfamiliar. He’s gonna need all the help he can get.”

 

***

 

Diggle showed up at Carly’s stoop at seven, ready for a nice, quiet evening on the town. It was really no big deal. They were friends first—family even—no, that was sorta incestuous, just friends. They would be having a simple dinner and yes, they had feelings for each other, but they would deal with those as mature, responsible adults. Carly was a mother, for Christ’s sake. They were going to be rational about this. He couldn’t see what Ollie and Felicity thought the big deal was.

 

Then Carly opened the door, her orange dress flowing up and down her like a waterfall at sunset, and he thought: oh. That’s what.

 

“Carly, you look… amazing.”

 

“You really like it?” Carly ran her hands over the fabric. “It’s been a while since I’ve dressed up. And it didn’t feel right to wear one of my old dresses, so I splurged a little on something new. Crazy, right?”

 

“No. It makes perfect sense.” Diggle took her hand. “So, where are we headed?”

 

“Uh, how about that new place, Club Darkside? I know it’s pretty exclusive.”

 

“Say no more, Carly. Being a bodyguard to the rich and famous has its perks.”

 

“You really think you can get us in?” Carly asked as he got the car door for her.

  
“Nah,” he grinned. “But it won’t hurt to try.”

 

***

 

Crouching on a nearby rooftop, Ollie heard everything. “Felicity, you get that?”

 

“Yeah. I’m hacking Darkside’s servers now—Oliver, I’m seeing zero openings.”

 

“Cross-check the list of reservations with the List.”

 

“Of what?”

 

“You know— _the_ List.”

 

“Oh.” Ollie heard a little digital ding over the line. “Here we go. Rashid Mahmoud. Owns a fleet of falafel food trucks.”

 

“What are they cover for? Drugs? Guns?”

 

“Nothing. They’re just really crappy falafels. Someone found a cockroach in one, but he paid the health inspector to cover it up.”

 

“Then I think it’s time he had _his_ health inspected.”

 

Ollie has rappelling down to his motorcycle when Felicity spoke up. “You’re going to give him first aid?”

 

“No. After I hurt him. Then he’ll need—a doctor.”

 

“Oh. That wasn’t clear.”

 

“They can’t all be winners.”

 

***

 

“RASHID MAHMOUD! YOU HAVE FAILED THIS CITY!”

 

“Please! Take anything! Just don’t hurt me!”

 

“I’m not going to hurt you. YOU are going to do something for me.”

 

“Name it! Anything, anything!”

 

“Cancel your reservation at Club Darkside?”

 

“What?”

 

“DO IT _NOW!_ ”

 

“Alright, alright, I’m calling!”

 

“GOOD. And if I find anymore cockroaches in your falafels, I’ll be taking more from you than a fine dining experience.”

 

***

 

“I can’t believe we got in,” Carly said, sitting down. They had a fine table overlooking the fire-pits where meat was cooked right before their eyes. It was close enough that Diggle took off his jacket. Carly could barely take her eyes off the spectacular surroundings to check the menu. “My goodness, everything looks so good—but so expensive--!”

 

“Get whatever you want,” Diggle told her. “My treat. It’s the least I can do after you spent so much money on your dress.”

 

“Oh, this? I got it on sale. It really wasn’t that expensive, honestly. Barely worth an appetizer in this place.”

 

The waiter came by, pleased at such a lovely couple’s patronage, or at least a convincing enough actor. He took their order, Diggle asking for a Lucanian ciambotta that had looked delicious when he’d seen Ollie eating one the other day and Carly ordering the house specialty: _le tube de la fleche_. Unfortunately, the waiter told her that the chef in charge of preparing it was out sick.

 

“Oh, that’s too bad. I’ve heard it is to die for.”

 

“Perhaps another time,” the waiter mollified. “If you would like more time to order, I will bring you some appetizers?”

 

“That would be wonderful, thanks,” Diggle said, opening his menu again.

 

Nearby, lurking behind a column, Ollie was dressed as a waiter. “Felicity, the woman wants _le tube de la fleche_ and she’s not getting it. This date is dead in the water.”

 

“Get into the kitchen. You’ll have to make it.”

 

“Felicity, I have trouble grilling a cheese sandwich.“

 

“Oh. I thought you ate raw plants because it was good for you… Don’t worry, I’ll talk you through this. First, toss the eggplant cubes with a teaspoon of salt…”

 

***

 

“Pardon me, Madame.” The second waiter had an odd beard and a strange accent. Carly wondered what part of France he was from. Did France have an equivalent to Minnesota? “It turns out our sous-chef was able to fill in and prepare _le tube de la fleche._ We apologize for the inconvenience; please, enjoy at your leisure, on the house.”

 

“Why, thank you. Thank you very much,” Carly said as he hustled off, the plate of bowls set down at their table. “You know, that waiter looked a lot like your boss.

 

“Really?” Diggle’s mouth was hidden behind his hand. “I didn’t see it.”

  
“Yeah, just with a Van Dyke.”

 

“Oliver Queen wouldn’t be caught dead in a Van Dyke.”

 

“I don’t know, I thought it looked pretty good on him.” Carly noticed Diggle looking away, almost like he was watching that waiter go. “John, what are you thinking about?”

 

“Huh? Oh, I don’t know—I suppose how odd it is to sit down and eat at a place like this instead of arrange security for it. Have to check myself to keep from counting exits.”

 

“My old warhorse.” A fire-pit flared up, sending up a mushroom cloud plume that hit the ceiling. There was light applause. “It is a bit much, though.”

 

“Yeah. Excepting the food, I might prefer Big Belly Burger.”

 

“We serve great food at Big Belly Burger.”

 

“And some of them come with the nicest toys…”

 

Carly whapped him with her napkin. “Jerk. But I see what you’re getting at.” She tried a bite of her meal; scrumptious. “Okay, this is better than a Big Belly Burger. I’d like to see them top our hand-spun milkshakes, though.”

 

“Of course they’d lose. Those smokestacks out on the floor would melt your shake before you could unwrap your straw.”

 

A laugh from Carly. Diggle felt old childhood butterflies working their way up his esophagus.

 

“Seriously now.” Carly set a delicate hand on the table linen. “Do you ever wish it was you, all Lifestyles on the Rich and Famous, sleeping fourteen hours a day and drinking champagne the other ten?”

 

“The sleep sounds nice. The rest of it? Honestly, no. It looks fine on the outside, but up close, you lose your taste for it.” He picked up his flute of champagne—a rare treat.

 

Not something you drank every day.

 

“Sounds like someone’s got a tell-all in him.”

 

“No, nothing too scandalous. Just that I see these people with so much, and it hardly ever seems to make them happy. Not that the people in the Glades have it made, or anything—everyone can have a hole in them—but poor people, they try to fill it with beer, drugs, a big TV. Rich people? They have all that—they try more and more to fill it. I prefer being where I am, being what I am. Simple man. Simple pleasures. Content. Uncomplicated.” Diggle tilted his head to the side. “That too Zen?”

 

“No, but I have a son in the sixth grade. I don’t know how much ‘uncomplicated’ I have to offer.”

 

“I could see myself like that kind of complication.”

 

***

 

Ollie sat on the rooftop, back in his costume, a skylight giving him a decent view of the restaurant, a better view of Diggle’s car. He kept glancing at it, almost wishing someone would try to key the thing so he could tag the asshole. No one tried. They were far from the Glades; this part of town didn’t see the kind of crime you fought with an arrowhead.

 

“You hearing this?” Felicity asked in his ear.

 

“Comms working fine,” he confirmed.

 

“No, I mean—is he kinda badmouthing you? It seems wrong, listening to him if he’s gonna badmouth—“

 

“He’s not talking about us.”

 

“But isn’t it true? Kinda? I mean, what if you can’t get off on fast cars and, Italian supermodels anymore, and this whole Hood thing is just a way to—I’m overstepping.”

 

“I invite criticism,” Ollie told her.

 

“No, I shouldn’t.”

 

“Felicity, if that’s what you think—“

 

“It’s _not_ what I think! I think it’s really brave, what you’re doing, but maybe there’s an ulterior—thing…”

 

“He’s not talking about me,” Ollie said, emphatic. “If anything, he’s talking about my cover. If he really thought I were some kind of thrillseeker, you really think he’d be helping us?”

 

“No. Suppose not. So, what’s it like in the hottest restaurant in town?” Felicity couldn’t be more obvious about wanting to change the subject if she played one of those disc jockey sound effects.

 

“Obnoxious scenery, fancy music, everyone wearing black, overpriced food. The usual.”

 

“Oh. Well, I don’t really know what the usual is. Why I asked, that’s—do you like pretending to be a millionaire playboy and hanging around places like that?”

 

“I am a millionaire playboy.”

 

“I know you are, but really-really, you’re the Hood… I mean, you’re really Oliver Queen, technically, but you’re really a guy who fights crime and works out with his shirt off, not somebody with—Italian cars and fast supermodels. I might have mixed that up.”

 

“No, sounded about right. I’ll be honest, it beats digging ditches—or working in an IT department.”

 

He could feel Felicity’s grin over the wire, like it shifted the electrons all by itself. “It wasn’t that bad over there. Just a little lacking in challenge?”

 

“Would you like it? Pretending to be a wealthy socialite, going to the hottest clubs, the coolest parties… meeting Paris Hilton…”

 

“You’ve met Paris Hilton?”

 

“I petted her dog.”

 

“Yeah, that sounds fun and all… but I suppose after a while—it’d be like a game, right? Seeing if anyone could spot you? But no one else is playing. Nobody cares, they’re not looking for an imposter. So maybe if someone were in on it…”

 

Yeah. Otherwise you’re just… lying.”

 

He heard a sudden whipcrack of typing over the line. “Hold up, Diggle’s on the move—they’ve finished their meal and Carly wants to go… wait, what’s ‘karaoke’?”

 

“You don’t know what karaoke is?”

 

“It’s not a sex position, is it?”


	2. Chapter 2

The Drop was more Diggle’s speed—a relaxed, Saturday night kinda place for people who were more interested in having a good time than being _seen_ having a good time. He didn’t have anything against Club Darkside, the meal had been excellent, but it wasn’t the kind of place you relaxed at. The Drop had a set of bead curtains that led into an arcade room, a bowling lane at the far side of another room, a dance floor, and a house band. Tonight, though, the only musicians were in the audience—only the aspiring were allowed to get on stage for Karaoke Night.

 

“Now this is nice,” Carly said. “I don’t think I’ve been here since Andy…”

 

Diggle took off his tie, tucking it into a pocket. “Shame about the music, though.”

 

On stage, an American Idol wannabe was doing undeserved things to Suspicious Minds.

 

“It’ll pick up,” she assured him. “Hey, you know, you don’t have to take my mind off him.”

 

“Andy?”

 

“Yeah. I wouldn’t be out on a date with you if I weren’t comfortable with—this.”

 

“I just don’t want to _make_ things uncomfortable.”

 

“You won’t. He was your brother, my husband, we both loved him. Honestly, I don’t mind being reminded of him. Yes, it hurts a little, even now, but that hurt just reminds me of how good it was when he was here. I don’t think he’d want me to forget that. I don’t.”

 

Diggle felt a smile pulling at his lips like a hand running over his skin. “I don’t either. But all things being equal, let’s work on making some new memories instead of going over the old ones?”

 

“Sounds good to me. You wanna dance?” A would-be high note crashed and burned instead. “Once Elvis has stopped spinning in his grave?”

 

***

 

Nearby, Ollie sat disguised in a ruffled knitwear sweater, his face hidden by a hat pulled low and a collar pulled high. Also, he had applied some eye shadow, which he thought was underrated as disguises went.

 

“Felicity, we need some better tunes if they’re going to dance—are you hearing this? If I told you a cat were being murdered on stage, would you doubt me?”

 

“I never doubt you. And I’m not surprised the singing’s bad, that club’s membership is eighty-four percent white.”

 

“Little racist, Fe.”

 

There was a brief pause, then she spoke apologetically: “My name’s Felicity. That’s okay, a lot of people forget it.”

 

Ollie frowned. “I didn’t forget your name, I just thought you could use a nickname. Friends call each other nicknames.”

 

“Oh. Right. Do you have a nickname?”

 

“Yeah, my friends call me Ollie—“

 

“I think I’ll call you Queequeg.”

 

Ollie’s response was flat, even by his standards. “What.”

 

“It’s short for Queen.”

 

“That’s longer than Queen.”

 

“And he’s a character from Moby Dick, so the both of you were in a shipwreck, it’s literary—why aren’t you stopping me from talking?”

 

“Felicity, tunes, now.”

 

“Right.” A quick clatter of typing. “Based on her visits to 8tracks, I’m going to say that her favorite song is I Say A Little Prayer. You know it?”

 

“Why would I need to know it?”

 

“Well, you’re going to sing it, right? You can’t just pay someone to sing it for you.”

 

“I’m a very rich man, Felicity.”

 

“Believe it or not, I can’t tell whether someone is a good singer by checking their browser history. If we’re going to do this, we have to do it ourselves. C’mon, you have a great voice, I love listening to you talk— _people_ love listening to you talk—“

 

“Felicity, I’m tone-deaf.”

 

“Tone-deaf?”

 

“I can’t sing.”

 

“Can’t sing?”

 

Ollie tapped his earpiece. “Is this thing repeating on me?”

 

“Oliver, everyone can sing.”

 

“ _Not me._ I can hit a bullseye at a hundred meters, I can beat up any three black belts, and I’m very good in bed. That’s my skillset. No singing.”

 

“Let me think—“

 

Someone got on stage to apparently punish a Nicki Minaj song for being a Nicki Minaj song, which should’ve already been punishment enough.

 

“ _Hurry,_ Smoak.”

 

“Okay, I’ve hacked into the place’s sound system, I can patch into the microphone—how good are you are lip-syncing?”

 

“What?”

 

“I have an excellent singing voice, Oliver. Obviously, I don’t sing in public because it’s nerve-wracking, but I should be fine doing it over the internet. Same principle as my take on Back To The Future. I could never argue that Marty McFly represents historical revisionism in the classroom face to face…”

 

“So you’re going to sing, and I’m going to pretend to be singing? Like Singing In The Rain?”

 

“Oh, I love that movie, it’s been so long since I’ve watched it—“

 

“It’s been a while for me too, but from what I can recall, they were both women in that movie.”

 

“Have I mentioned I have a very masculine singing voice, Oliver?”

 

***

 

Diggle happened to look at the stage as the next singer came up. Carly noticed.

 

“Are you alright, John? You look pale, and that’s a neat trick for a black man.”

 

***

 

The emcee had already taken a quick selfie with Oliver. Now, he hyped him, dreaming of The Drop trending in the next five minutes. “Alright everyone, we’ve got a special treat for you tonight! Starling’s own Oliver Queen is going to sing for us, _right, now!”_

 

A plethora of smartphones appeared as if by magic, their screens reflecting Ollie like backwards mirrors as he approached the microphone.

 

“Hello,” he said stiffly. “Do you like music? I… like music. Let’s do some music. Now.” He tapped on the microphone. “Testing, one-two, one-two, one-two, one-two…” There was a hiss of static. “Okay. Musi—“

 

He was interrupted by a sudden stir of Burt Bacharach piano playing. Ollie nodded along, trying to remember how the song went, jumping in just as he heard Felicity start.

 

“The moment I wake up/Before I put on my makeup…”

 

***

 

Carly was already shimmying in her seat a little. “Your boss has good taste. This is my jam! He’s surprisingly falsetto, though.”

 

“It’s like the Bee Gees,” Diggle told her. “White man who sings like a black girl. You wanna dance?”

 

***

 

Somewhere in the Glades, Felicity sang her heart out, always remembering that Christina Aguilera wouldn’t be afraid to sing pretending to be her male boss so that her best friend could have a nice date.

 

***

 

Carly hadn’t been a nun after Andy died. She tried to put herself out there, date as best she could with an equally grief-stricken son who needed her. They weren’t all jerks, either. A lot of them were patient, understanding. But she kept comparing them to Andy—his love for her—his rightness for her—and she’d felt pathetic, trying to substitute one for the other.

 

Dancing with John didn’t feel pathetic… that felt good. That felt right.

 

And from the look in his eyes, she could tell John felt the same way. She hoped he could tell from her eyes as well. It wasn’t like he was looking anywhere else.

 

***

 

 _Jazz hands,_ Oliver Queen thought. _The key to good lip-syncing is the precise application of jazz hands…_


End file.
